Ethyl 4-piperidinecarboxylate → ethyl N-(2,6-dimethoxyphenylmethyl)piperidin-4-ylcarboxylate

HRID 1683837Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1683837
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[CH2:11]Br.[NH:13]1[CH2:18][CH2:17][CH:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:15][CH2:14]1.[F-].[K+]>C(#N)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[CH2:11][N:13]1[CH2:18][CH2:17][CH:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:15][CH2:14]1

Komponenten

5

Edukt 3

HCID 70770Ethyl 4-piperidinecarboxylateHCID 522689Potassium FluorideHCID 155569582-(Bromomethyl)-1,3-dimethoxybenzene

Produkt 1

HCID 19040928ethyl N-(2,6-dimethoxyphenylmethyl)piperidin-4-ylcarboxylateAusbeute 16,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A stirred solution of 4.7 grams (0.020 mole) of 2,6-dimethoxyphenylmethyl bromide, 3.2 grams (0.020 mole) of ethyl piperidin-4-ylcarboxylate, and 23.5 grams (0.200 mole) of 50% potassium fluoride on Celite® filter aid in 100 mL of acetonitrile was heated at reflux for about 18 hours, after which the reaction mixture was cooled and filtered. The filtrate was concentrated under reduced pressure to a residue, which was subjected to column chromatography on silica gel, with mixtures of ethyl acetate in hexane as eluants. The product-containing fractions were combined and concentrated under reduced pressure to a residue. The residue was analyzed using thin layer chromatography, which indicated that the residue was impure. The residue was again subjected to column chromatography on silica gel, with mixtures of ethyl acetate in hexane and methanol in ethyl acetate as eluants. The product-containing fractions were combined and concentrated under reduced pressure, yielding about one gram of ethyl N-(2,6-dimethoxyphenylmethyl)piperidin-4-ylcarboxylate. The NMR spectrum was consistent with the proposed structure.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for about 18 hours
  3. temperatureafter which the reaction mixture was cooled
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure to a residue, which
  6. concentrationconcentrated under reduced pressure to a residue
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a139f7783188480298cdfc3e564ac19e
Quelldatensatz
uspto-grants-1997_06
Patentnummer
US05639763

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